75726-96-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-N-isopropylacetamide is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to introduce diverse functional groups through substitution reactions. The presence of the bromo group allows for the incorporation of different functional groups, enhancing the reactivity and selectivity of the synthesized compounds.
Used in Organic Synthesis:
2-Bromo-N-isopropylacetamide is used as a versatile building block in organic synthesis for its ability to facilitate the introduction of functional groups and the formation of new chemical bonds. The isopropyl group provides steric hindrance, which can influence the reactivity and selectivity of certain reactions, making it a valuable component in the development of complex organic molecules.

InChI:InChI=1/C5H10BrNO/c1-4(2)7-5(8)3-6/h4H,3H2,1-2H3,(H,7,8)

Upstream product

• 75-31-0 isopropylamine 
• 598-21-0 2-Bromoacetyl bromide 
• 71985-62-1 2-benzenesulfonyl-2-bromo-1-isopropyl-aziridine 
• 22118-09-8 2-bromoacetyl chloride 
• 79-08-3 bromoacetic acid 

Downstream Products

• 38265-81-5 Dithiophosphoric acid O-ethyl ester S-(isopropylcarbamoyl-methyl) ester S'-(2-methoxy-ethyl) ester 
• 38265-82-6 Dithiophosphoric acid S-(2-ethoxy-ethyl) ester O-ethyl ester S'-(isopropylcarbamoyl-methyl) ester 
• 151965-03-6 2-Benzyloxyamino-N-isopropyl-acetamide 
• 104241-10-3 C₅₉H₉₁N₁₈O₂₂S₃⁽¹⁺⁾*HO₄S^(1-) 
• 51489-14-6 N-isopropyl-2-methylamino-acetamide 
• 496018-68-9 GTC-268925 
• 445266-27-3 GTC-268776 
• 710355-36-5 1,2-dimethyl-3-(2-propyl)imidazolidin-4-one 
• 1039749-45-5 (+/-)-4,4-dicyano-1-isopropyl-5-phenylpyrrolidin-2-one 
• 1192358-66-9 2-azido-N-isopropylacetamide 

Relevant academic research and scientific papers

In Vitro Anti-Toxoplasma gondii Activity Evaluation of a New Series of Quinazolin-4(3H)-one Derivatives

Toxoplasmosis post serious threaten to human health, leading to severely eye and brain disease, especially for immunocompromised patients and pregnant women. The multiple side effects and long dosing period of current main treatment regiments calls for high effective and low toxicity anti-toxoplasmosis drugs. Herein, we report our efforts to synthesize a series of 2-(piperazin-1-yl)quinazolin-4(3H)-one derivatives and investigate their activity against Toxoplasma gondii tachyzoites in vitro based on cell phenotype screening. Among the 26 compounds, 8w and 8x with diaryl ether moiety at the side chain of piperazine exhibited good efficacy to inhibit T. gondii, with IC50 values of 4 μM and 3 μM, respectively. Structure-activity relationship (SAR) studies implies that hydrophobic aryl at the side chain would be preferred for improvement of activity. Molecular docking study reveals these two compounds appeared high affinity to TgCDPK1 by interaction with the hydrophobic pocket of ATP-binding cleft.

Synthesis method of SLx-2119

The invention belongs to the field of drug synthesis, and particularly, discloses a synthesis method of SLx-2119, wherein the synthesis method comprises the steps: firstly, with isopropylamine and bromoacetyl bromide as raw materials, preparing 2-bromo-N-isopropyl acetamide I, and then successively carrying out nucleophilic substitution reaction and ester hydrolysis reaction with 3-methyl hydroxybenzoate, carrying out amination reaction, cyclization reaction and chlorination reaction with 2-aminobenzamide, and finally carrying out nucleophilic substitution reaction with 5-aminoindazole, to prepare the SLx-2119. The use of expensive dihydroxy phenyl borate, Pd(dppf)Cl2, 2,4-dihydrogen quinazoline and other reagents is avoided, so the costs are reduced; the use of heavy metal palladium is also avoided, so the synthesis method has the advantages of no heavy metal pollution, environmental friendliness, raw materials without heavy metal residues, short reaction route, high yield and low cost, and is beneficial for industrialized production.

TREATMENT OF GVHD

The invention relates to treatment of graft versus host disease (GVHD) using compounds that inhibit ROCK2. In preferred aspects, the present invention provides methods for the treatment of GVHD, including chronic GVHD ( cGVHD) using compounds having the formulae l-XXV, as set forth herein.

AUTOTAXIN INHIBITOR COMPOUNDS

Described herein are compounds that are autotaxin inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with autotaxin activity.

TREATMENT OF OCULAR DISORDERS

The invention provides methods of treatment of ocular disorders, including ocular disease with an angiogenic component. In certain embodiments, the treatment comprises administration of a ROCK2 inhibitor and an angiogenesis inhibitor. In certain embodiments, the ROCK2 inhibitor is ROCK2 selective. In certain embodiments, the angiogenesis inhibitor is a VEGF antagonist, for example, and VEGFR2 antibody.

α-Aminoamides as ligands in Goldberg amidations

α-Aminoamides are shown to be useful as ligands in Goldberg amidations. A number of α-aminoamides are examined and the importance of substitution on the α-aminoamides is explored. Acetamide is focused on as the nucleophilic coupling partner due to its low cost, stability and convenience as a protecting group. The initial substrate scope for these catalysts is explored and includes electronically activated and deactivated aryl bromides, however o-substituted aryl bromides are problematic.

Salicylic acid based small molecule inhibitor for the oncogenic src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2)

The Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) plays a pivotal role in growth factor and cytokine signaling. Gain-of-function SHP2 mutations are associated with Noonan syndrome, various kinds of leukemias, and solid tumors. Thus, there is considerable interest in SHP2 as a potential target for anticancer and antileukemia therapy. We report a salicylic acid based combinatorial library approach aimed at binding both active site and unique nearby subpockets for enhanced affinity and selectivity. Screening of the library led to the identification of a SHP2 inhibitor II-B08 (compound 9) with highly efficacious cellular activity. Compound 9 blocks growth factor stimulated ERK1/2 activation and hematopoietic progenitor proliferation, providing supporting evidence that chemical inhibition of SHP2 may be therapeutically useful for anticancer and antileukemia treatment. X-ray crystallographic analysis of the structure of SHP2 in complex with 9 reveals molecular determinants that can be exploited for the acquisition of more potent and selective SHP2 inhibitors.

Targeting mycobacterium protein tyrosine phosphatase B for antituberculosis agents

Protein tyrosine phosphatases are often exploited and subverted by pathogenic bacteria to cause human diseases. The tyrosine phosphatase mPTPB from Mycobacterium tuberculosis is an essential virulence factor that is secreted by the bacterium into the cytoplasm of macrophages, where it mediates mycobacterial survival in the host. Consequently, there is considerable interest in understanding the mechanism by which mPTPB evades the host immune responses, and in developing potent and selective mPTPB inhibitors as unique antituberculosis (antiTB) agents. We uncovered that mPTPB subverts the innate immune responses by blocking the ERK1/2 and p38 mediated IL-6 production and promoting host cell survival by activating the Akt pathway. We identified a potent and selective mPTPB inhibitor I-A09 with highly efficacious cellular activity, from a combinatorial library of bidentate benzofuran salicylic acid derivatives assembled by click chemistry. We demonstrated that inhibition of mPTPB with I-A09 in macrophages reverses the altered host immune responses induced by the bacterial phosphatase and prevents TB growth in host cells. The results provide the necessary proof-of-principle data to support the notion that specific inhibitors of the mPTPB may serve as effective antiTB therapeutics.

RHO KINASE INHIBITORS

The present invention relates to inhibitors of ROCK1 and ROCK2, which may be selective for ROCK2, and methods of modulating the pharmacokinetic and/or pharmacodynamic properties of such compounds. Also provided are methods of inhibiting ROCK1 and/or ROCK2. Also provided are treatments combining inhibitors of ROCK1 and/or ROCK2 with statins.

Structure-activity relationships of 9-substituted-9-dihydroerythromycin- based motilin agonists: Optimizing for potency and safety

A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties. 2009 American Chemical Society.